N-(2,2,3,3,3-pentafluoro-n-propyl)norcodeine methanesulfonate | 123241-02-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: N-(2,2,3,3,3-pentafluoro-n-propyl)norcodeine methanesulfonate
• CAS: 123241-02-1
• 化学式: CH₄O₃S*C₂₀H₂₀F₅NO₃
• 分子量: 513.483
• InChiKey: CBZIQHUTZIZZDI-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-(2,2,3,3,3-pentafluoro-n-propyl)norcodeine methanesulfonate 在 甲烷磺酸 作用下， 反应 1.0h， 以39%的产率得到N-(2,2,3,3,3-pentafluoro-n-propyl)norapocodeine
  参考文献：
  名称：

  Synthesis and structural requirements of N-substituted norapomorphines for affinity and activity at dopamine D-1, D-2, and agonist receptor sites in rat brain

  摘要：

  A series of N-substituted analogues of (R)-(-)-norapomorphine were synthesized to study the optimal structural requirements of the N-alkyl side chain to interact with D-1 and D-2 dopaminergic receptors as well as dopamine (DA) agonist binding sites. Evaluations included testing the affinity of these compounds for DA receptor sites in rat striatal tissue and assessing stereotypy as a behavioral index of dopaminergic activity. The electronic, steric, and lipophilic properties of the N-alkyl side chain were found to be related to affinity, D-2 selectivity, and dopaminergic activity. All 11 compounds evaluated had relatively low affinity at D-1 sites. Optimum D-2 and agonist-site affinity as well as agonist activity were exhibited by N-cyclopropylmethyl (7) greater than or equal to N-allyl (8) greater than or equal to N-propyl (4) or N-ethyl (3) substituted compounds. Branching of the N-alkyl side chain as in N-isopropyl (5) and N-isobutyl (6) markedly reduced the D-2 affinity and activity, presumably due to steric effects. The N-trifluoroethyl (10) and N-pentafluoropropyl (11) derivatives had low affinity for all their dopamine receptor sites and no agonistic activity; evidently, the highly electronegative F atoms decrease basicity of the N atom and therefore decrease the ability of the N atom to be cationic at physiological pH, a proposed requirement for high-affinity binding to DA receptors.

  DOI：

  10.1021/jm00163a007